


Pretty and Dangerous Go Well Together

by stinkylemons131



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, BAMF Stiles, Blow Jobs in a Car, Boss Derek Hale, Cock Slut Stiles Stilinski, F/F, F/M, M/M, Mafia Derek, Oral Sex, Porn With Plot, Pretty Stiles, Smut, Stiles Stilinski is a Tease, Top Derek Hale/Bottom Stiles Stilinski, hot Stiles
Language: English
Status: Completed
Published: 2020-09-10
Updated: 2020-09-13
Packaged: 2021-03-06 17:20:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,374
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26392543
Author URL: https://archiveofourown.org/users/stinkylemons131/pseuds/stinkylemons131
Summary: Stiles meets Derek Hale, one of the most powerful mafia bosses in New York. Porn with plot if you squint.
Relationships: Aiden/Ethan/Jackson Whittemore, Allison Argent/Lydia Martin, Derek Hale/Stiles Stilinski, Scott McCall/Malia Tate, Vernon Boyd/Erica Reyes
Comments: 8
Kudos: 323





	1. Chapter 1

Stiles swayed his slender hips to the deep vibrating beat of the song playing through the huge speakers in the bar. It was a bar he frequented mostly on his weekends, having college on the weekdays. He came here to relax and maybe even find a man to spend many of his nights together. So it wasn’t unexpected when he felt large hands grip each side of his waists. He let the man choose the rhythm they danced at and went with the flow, not even looking back to see the face of the tall man he was dancing with. 

Stiles was a boy who had a feminine body, an hourglass-like body. Hips wide with a tiny waist. Most guys liked that on him, they would grab his hips so hard leaving bruises that lasted for days. Not that Stiles minded. You could say it was one of his kinks. He loved looking at his body the next day, looking at the love bites left behind. Another part of his body men liked were his moles, they covered nearly his whole body. They all paid special attention to them, covering them with their tongues making him tremble under their much bigger bodies.

He didn’t flinch when he felt hands slide down his thighs, he revelled in the feeling of being the centre of attention of this no doubt gorgeous man. He moaned lavishly when he felt lips on the junction of his neck, one of his weak spots. The man’s chuckle caused his knees to go buckle, it was deep and raspy, just what Stiles liked. 

“You up for a night of fun baby boy?” 

Stiles gasped in surprise when he was suddenly spun around to look at the man he had been dancing with. His mouth opened wide in shock. The man who stood in front of him was Derek Hale, the infamous criminal. He was mafia boss to the ‘Hale Pack’. They were called that as it was said that the deaths they had caused made the victims look like they had been mauled by wolves from deep in the forest. 

Derek Hales was a man of six foot. Black stubble covered his chin, giving him a chiselled look. His jawline was so straight it could slice a man down with one hit. His hazel-green eyes shimmered in the flashing lights of the club. He looked every part of a mafia boss. Leather jacket, a gun handle could be seen at the side of the waistband of his trousers. 

Stiles always like a bit of danger with his fun. 

“Guess we’ll have to see if you can satisfy me, Hale,” Stiles grinned showing a manic side to him, the danger excited him. He wanted more, wanted Hale to show him what he could do. 

Derek growled in anger as the boy defied him. He grabbed Stiles closer towards him, by his waist, and smashed their lips together. He used Stiles surprise as an opportunity to grab the delicious ass he had been eyeing the whole time, pushing his tongue into Stiles’s mouth when he gasped in pleasure. Stiles immediately backed down and let Derek’s warm tongue explore his mouth. His body trembled when Derek sucked on his tongue with his mouth. He couldn’t wait for more.

Stiles whined in displeasure as Derek separated their lips, instead taking his hand and leading him towards the exit of the club. Stiles couldn’t help but feel anticipation about what was going to come next. A night with one of the biggest mafia bosses in New York. He couldn’t wait! If only he could keep the man wrapped around his finger forever. 

Unsurprisingly, there was a black limo parked outside the club. There was a huge man standing beside it, no doubt one of Hale’s underlings.

“Where to boss?” The man asked Derek as they walked quickly towards him.

“The house, take the quick way. I want to be there as soon as possible, got it?” Derek ordered him in a growl as he tightened his grip on Stile’s hand.

“Of course boss,” The man replied and the three of them got inside the vehicle. Stiles and Derek in the back and the man driving.

Stiles was immediately put onto Derek’s lap as they got inside. The drinks he had drunk earlier finally hitting softly, just a buzz, as he started to grind slowly onto Derek’s lap. He heard Derek growl in approval as he made circular movements with his hips, Derek’s arousal making itself known. Stiles hands reached for Derek’s belt but before he could undo the pants, Derek stopped him.

“You've got to ask before you take baby boy,” The mafia boss said whilst grinning at Stile’s displeasure at those words. 

“Make me,” Stiles said in response.

Stiles whimpered suddenly when his hair was gripped tightly, Derek pulling it downwards. His body arched into Derek’s as the grip got tighter. 

“You want to play like that huh baby? Don’t regret it afterwards.” Hale whispered into Stiles' ear making him shiver with regret. He was playing with fire, who's to say he wouldn’t get burnt. Stiles watched as Derek slowly unbuckled his trousers making Stiles wait even longer to get his mouth on Derek’s cock. 

Derek pushed Stiles down into the floor of the car behind the driver's seat. He let his trousers sit at his ankles, wanting Stiles to do everything else.

“Just nice and slow baby.” 

Stiles whined in need as he mouthed at Derek’s clothed cock, feeling it swell under his ministrations. He loved it when men became aroused because of him, it made him feel powerful. He loved being the one handing out the pleasure. He gripped the top of Derek’s boxers with his teeth and slowly pulled them down, freeing Derek’s long, thick cock. He moaned at the sight of the member standing tall. 

He licked a stripe from the bottom of Derek’s cock to the tip, sucking the head into his mouth. He licked the slit of the head, sucking harder when he heard Derek praising him. He made eye contact with Derek seconds before taking the nine-inch dick whole. 

Derek moaned as his cock hit the back of Stiles throat. He gripped Stiles hair once again, moving Stiles head back and forth slowly getting faster before the pace became brutal. Stiles eyes watered as the cock forcefully made its way in and out of his mouth. He moaned around it causing vibrations to go through it. Derek groaned as he came into Stiles mouth, filling it up with his thick seed. 

Stiles swallowed it as it overflowed in his mouth, moaning at the salty taste of the Mafia bosses semen. Then Stiles and Derek became aware of the fact that the limo had stopped already, meaning they were already at the house. 

Derek ripped the door open and lifted Stiles into arms as he made his way into the house, jogging lightly up the stairs towards his room. When he got there he threw Stiles onto the bed and made sure to lock the door before making his way to Stiles who was laying down on the bed with his legs spread as if waiting for Derek to come and lay between them. He did just that, grabbing Stiles legs and lifting them up over his shoulders. 

Derek helped Stiles shimmy out of his tight-fitting jeans, getting impatient. He ripped off Stiles underwear, immediately taking Stiles length into his mouth. Stiles yelled in surprise and pleasure as his cock was taken in by Derek's heat. 

“Ah-hh-h D-Derek please keep going” Stiles whined.

His body arched off of the bed and Derek's pace got faster, but before he could cum Derek stopped and instead moved his mouth towards Stiles twitching slutty hole. Derek licked his lips before reaching over to Stiles mouth with his index finger. 

“Suck” He commanded 

Stiles followed the command, lathering the finger with copious amounts of saliva, moaning as he did. Derek pulled his finger out and then circled Stiles hole with it. He forced his index finger in, breathing in Stiles loud whimpers that he was causing. Derek grinned as his finger bent and Stiles prostate straight on. He slowly pushed in another digit whilst he grabbed the bottle of lube he had had in his jacket pocket, pouring it over Stiles hole and his fingers. It made everything a lot smoother and let his fingers move quicker in Stiles.

“Fuck baby, you’re so tight around my fingers, squeezing me constantly. You’re perfect for me” Derek growled into Stiles ear, making his way down Stiles neck with his teeth. He left bites and hickeys down Stiles slim neck that was presented to him. This boy was his, not that Stiles knew it yet. 

Stiles groaned as he felt the head of Derek’s member touch his hole, Derek looked to Stiles for consent who nodded and continued to push his cock into Stiles warm cavern. Derek moaned loud as Stiles' heat surrounded his cock, squeezing him for all he was worth. 

“Remembered when you disobeyed me? I’m going to make you regret it, baby boy.” Derek growled menacingly as he started with brutal thrusts into Stiles smaller body. His big cock stretching Stiles hole to his limits.

“Derek, f-faster p-lease.”

“What's my name, my proper name?” Derek stopped moving as he whispered into Stiles' ear. 

“D-Daddy.” Stiles whimpered in greed as he wanted more of the huge cock that was giving him so much pleasure. 

“Good boy, you’re doing so well.” Derek smiled as he started thrusting again, making Stiles legs shake with the force of the thrusts. Stiles whimpered at the praise, the cock was making him go crazy. It was the best he had ever had before. 

Derek thrusts started quickening as he felt the feeling build up in his cock. He made a few last brutal pushes of his hips making Stiles scream out in pleasure as he came with Derek. Derek filled up Stiles deep inside making Stiles whimpered as he felt his stomach bulge. Derek pulled out as he saw Stiles eyes about to flutter close.

“You’re mine now baby boy forever.” The mafia boss whispered into Stiles ear grinning as he saw Stiles fall asleep in his arms who had subconsciously wrapped his limbs around Derek’s much larger body. Derek soon fell asleep too whilst watching Stiles chest move up and down to the beat of his heart.


	2. Chapter 2

**Summary for the Chapter:**

> Pretty gets dangerous

After meeting Derek at the club and going on many dates afterwards, Derek had asked Stiles to be his boyfriend which he obviously said yes to. Who wouldn’t have? In those few months, Stiles had learned a lot about his boyfriend and his job. The man who had been driving the car was called Boyd, he had a girlfriend called Erica who was also in Derek’s mafia. Then there was Allison who was dating Lydia, Scott who was dating Malia, Jackson who was dating Ethan and Aiden. But of course, Stiles didn’t judge their decisions. He had become quite close with everyone especially Scott who was now like a brother to him. 

Stiles had learned how far Derek would go for him when he had been suddenly kidnapped one day by one of their enemies, Deucalion. Derek had ripped apart each and every person part of Deucalion’s mafia all by himself for Stiles. There was no way he could ever leave Derek now, not that he wanted to though. One of the hottest advantages about having a mafia boss as a boyfriend Stiles thought was definitely when Derek got all dangerous with his enemies. He would pull out his gun or whatever weapon he thought best and point it right between his enemies eyes. But it was really the whisper of the threats that got Stiles hot and heavy. 

That's why he was now in this predicament. It was all his boyfriend's fault of course that he now wanted to just have Derek push him onto his desk and ravish him. But of course, he couldn’t have that because Derek was having to deal with this stupid man who couldn’t get his customer to pay the full price for the drugs he had been selling. Stiles was getting impatient. He was going to have to do something about this himself. He got the attention of Boyd who was standing in the corner of the room and got him to walk over to him.

“Go get me the biggest kitchen knife we have and don’t let Derek see.” He asked Boyd, whispering so Derek wouldn’t know what he was about to do.

Once Boyd had come back with the knife and had given it to Stiles, he waited silently for his moment. Knowing the shitty men that Derek worked with, it would come soon.

“If you just want more money why don’t you sell your slut to some old men, I’m sure he AND the old men would just love it, wouldn’t you slut?” The man sitting in the chair said it directly looking at Stiles, what a mistake that was. Stiles was just going to have so much fun.

Derek shouted in anger as the man insulted his boyfriend, about to immediately kill the man but Stiles stopped him before he could. Derek looked at Stiles in shock, he didn’t know why Stiles stopped him but it was obvious they were about to find out. Stiles slowly stalked his way towards the man named Josh. 

“You would have just loved to see this ass being fucked by multiple men wouldn’t you, Josh?” Stiles whispered to the man whilst taking a seat directly on the man's lap, hiding the knife behind his back. Derek growled possessively when he saw the man place his hands on his boyfriend's ass. 

“Too bad you won’t be alive,” Stiles said, shocking the man who instantly lifted his hand to the gaping hole in his neck that had been caused by Stiles immediately after he had placed his hands on Stiles. Stiles looked on in disgust as his clothes had been ruined by the man's blood. He lifted himself off the man's lap and made his way towards Derek.

“Do you have time for me now daddy?”

**Notes for the Chapter:**

> This is gonna be the last chapter

**Author's Note:**

> I hope you enjoyed it   
> kudos and comments are welcome x


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